Triethylamine → HCID 68996976, compound

HRID 1821392Notes

Reaction equation

HRID 1821392 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:15]=[CH:14][C:13]=2[NH2:24])=[N:2]1.C(N(CC)CC)C.[CH3:32][N:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:38]([Cl:40])=[O:39].C(=O)([O-])O.[Na+]>C1COCC1>[ClH:40].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[C:16]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[CH:15]=[CH:14][C:13]=2[NH:24][C:38]([C:34]2[N:33]([CH3:32])[CH:37]=[CH:36][CH:35]=2)=[O:39])=[N:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27950921-Methyl-1H-pyrrole-2-carbonyl chlorideHCID 690043002-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine

Product 1

HCID 68996976HCID 68996976, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[2-(1H-indazol-3-yl)vinyl]-4-(morpholin-4-yl)phenylamine (0.30 g, 0.94 mmol) synthesized in Example 225 was dissolved in THF (10 mL) and the solution was added with triethylamine (0.40 mL, 2.9 mmol) and N-methylpyrrolecarbonyl chloride (0.41 g, 2.8 mmol), followed by stirring at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure to obtain free base of Compound 226. Further, said free base was treated by 4 mol/L hydrogen chloride-methanol solution (1.0 mL) to obtain Compound 226 (0.23 g, 49%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45e5a1e66fe14058a5dcdaa2fdd255ec
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…